Mystery Guys and Pity Dates
by Eileen
Summary: AU-a little holiday story of missed opportunities and attempted matchmaking, told in answering machine messages.


_(So I was listening to "Christmas Wrapping" for the fourth time (I work retail and have no choice) when this idea sort of popped into my head. Enjoy!)_

* * *

"Hey, this is Dean. I'm not available right now. Leave a message at the beep."

BEEP!

"Hey, Dean, it's Sam. Listen, I need you to do me a favor. Can you go pick up my order from the tea shop and bring it to me at the library? It should be ready by the time you get there. Oh, and by the way, Gabe wants to set you up with his brother. Now, don't go getting all indignant on me. From what I hear, he's really a nice guy. I was thinking of having the four of us go out to dinner one night this week, maybe next. I know it's really busy with the holidays and all, but Gabe really wants you to meet his brother. Give the guy a chance, okay? Call me."

BEEP!

"Sam? I've got your ridiculously complicated tea, and I'm sitting outside in the car waiting for you to come get it. I'm in the parking lot right next to the book drop. Anyway . . . I kind of met someone while I was in there. We got to talking and hit it off and he gave me his number and I'm hoping we can see each other again soon, but you know how crazy my schedule is. We'll talk about it when you come out here and get your goddamn tea, okay?"

BEEP!

"Hey, Dean? What's going on with you and Tea-shop Guy? Cause Gabe's brother is still single, but from what I hear, he might have met someone, so hurry or you'll lose your chance. You're coming to Easter dinner, right? Gabe's brother will be out of town on business, but we can set something up for the following week. Or whatever's good for you. Call me."

BEEP!

"Sam, I wish you and Gabe would back off about me going out with his brother. I'm sure he's a nice guy and all that, but I'm trying to get hold of-what did you call him? Tea Shop Guy? Yeah, I keep calling and missing him. Then he calls back and misses me. It's like whenever I have a free moment to go do something, he's in the middle of something else. Things have got to settle down soon. So no more matchmaking, okay?"

BEEP!

"Dean, this is Cas. Again. I thought you said in our last conversation that you're free this weekend. We're putting the boat in the water-it's partly mine, partly my brother's. He and his better half will be along, and I was hoping you could come. Call me as soon as you get this."

BEEP!

"Hey, Cas. Listen, man, I'm gonna have to take a raincheck on the boat thing. I went to the beach with my brother and the guy he's seeing, and I kinda forgot the sunscreen. It hurts when I **breathe**. I'm gonna take some aspirin and lie down-if I can find a comfortable position, that is. Man, I'm sorry. I'll make it up to you. Love you."

BEEP!

"Sam? Just wanted to let you know that I'm not gonna be able to make it to Gabe's Halloween party because I'm going to another party with my guy. Some friend of his from college or something. We have matching costumes and everything, we look like total dorks. I'll send you pictures. Later, bro."

BEEP!

"Dean, this is Cas. I hope you're not disappointed, but we won't be making it to the party after all. My car wouldn't start, and when I called the auto club, the man said that the whole transmission was blown. So now I'm waiting for a tow truck, and even if I borrowed a car and came right now, we'd never make it. I'm sorry that these things keep happening to us. I'll call you when I can."

BEEP!

"Dean, I've had it. Both of us have had it. You keep talking about this mystery man of yours, but neither of us have seen him, and from what you've been telling me, it sounds like you two haven't been on an actual date yet. So I'm giving you an ultimatum: either bring Mystery Guy to Christmas dinner with you, or we'll have no choice but to have Gabe's brother here waiting for you. Your choice. See you at two."

BEEP!

"Cas? Listen, my brother and his boyfriend are getting tough with me. They're determined to set me up with this brother of his. I'm sure he's a nice guy, but I hate the thought of them setting us up because they think I can't get a date any other way. They think I'm making you up. Will you please come with me to my family's Christmas dinner? It would really mean a lot to me. We'll spend every other holiday with your family from now on, but I need to prove to my brother and the guy he's dating that I'm not a loser who has to make up a boyfriend just to get out of pity dates. Please? Dinner's at two, so pick me up at one-thirty. Okay? Love you."

BEEP!

"Hello, Gabriel. Listen, I'm afraid I won't be coming to dinner with you and your friend after all. The guy I've been . . . sort of seeing . . . needs me to come with him to his family dinner. I'll see you New Year's Eve. Don't try and get me drunk this time. I mean it."

BEEP!

"Hey, Charlie, it's Dean. I know you and your girls are in the middle of dinner, but I just had to tell you. You're gonna laugh when you hear this. So you know that guy I met at the tea shop last year, that I've been trying to get together with but something always comes up? Meanwhile Sam and his boyfriend are trying to set me up with this brother of his, and I'm avoiding the subject. Well, they laid down the law, so I called my guy and told him that I really needed him to come to Christmas dinner with me.

"So we got to Sam's house and went up and rang the bell, and Gabe answers the door, and he looks at Cas and says, 'I thought you weren't coming.' And then Sam comes out and he's like, 'Wait a minute, this is your mystery guy?' And it took us a minute to figure it out. Yeah. Pity Date Brother-the guy I've been avoiding all year-is also the guy I've been trying to hook up with all the same time! It's so funny, cause I knew he had a brother, and he knew I had a brother, we just didn't know that our brothers knew each other.

"Anyway, I won't keep you any longer. That old Christmas magic, huh? Talk about a happy ending. See you soon, kiddo."

BEEP!

"Sam? It's Charlie. You owe me twenty big ones, pal. I take cash, check, or coffee shop gift certificates. Who knows, I may meet my mystery person there. Merry Christmas, bitches."


End file.
